Pros
City Year is a fun and fulfilling experience. You work as a team, have a ton of support from your supervising corps member and program manager, as well as from other corps members. You received a living stipend which is enough to live off of, and quite frankly it looks great on your resume/CV. This position will open many doors for you if you're not sure of what you want to do, but are interested in teaching, social work or humanities.
Cons
The public "physical training" is quite embarrassing. You are required to do jumping jacks and other exercises in public spaces while shouting chants. It was unnecessary. Also, you do not choose the school or team you will be assigned to. Sometimes the schools do not provide much integration for the City Year team among the school community.